Journal of Natural Products 最新文献

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Halogenation-Guided Chemical Screening Uncovers Cyanobacterin Analogues from the Cyanobacterium Tolypothrix sp. PCC9009 卤化引导的化学筛选揭示了蓝藻中类似物的蓝藻细菌来自topothrix sp. PCC9009。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-12 DOI: 10.1021/acs.jnatprod.5c00591
Franziska Schanbacher, , , Arthur Guljamow, , , Valerie I. C. Rebhahn, , , Peter Schmieder, , , Heike Enke, , , Elke Dittmann, , , Martin Baunach, , and , Timo H. J. Niedermeyer*, 
{"title":"Halogenation-Guided Chemical Screening Uncovers Cyanobacterin Analogues from the Cyanobacterium Tolypothrix sp. PCC9009","authors":"Franziska Schanbacher,&nbsp;, ,&nbsp;Arthur Guljamow,&nbsp;, ,&nbsp;Valerie I. C. Rebhahn,&nbsp;, ,&nbsp;Peter Schmieder,&nbsp;, ,&nbsp;Heike Enke,&nbsp;, ,&nbsp;Elke Dittmann,&nbsp;, ,&nbsp;Martin Baunach,&nbsp;, and ,&nbsp;Timo H. J. Niedermeyer*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00591","DOIUrl":"10.1021/acs.jnatprod.5c00591","url":null,"abstract":"<p >Halogenated specialized metabolites show high chemical diversity and exhibit a range of biological activities. A targeted screening of a cyanobacteria extract library for halogenated specialized metabolites using HPLC-HRMS combined with MassQL and Haloseeker indicated that several of the extracts contained halogenated compounds, among them an extract of <i>Tolypothrix</i> sp. PCC9009. This freshwater cyanobacterium has been known since the early 1980s for producing the chlorinated specialized metabolite cyanobacterin, containing a γ-lactone core structure with a hydroxy group that is essential for its herbicidal activity against cyanobacteria and green algae. Mass-spectrometry-based molecular networking was employed to explore the chemical space of natural cyanobacterin analogues. This analysis led to the identification of 15 previously unknown compounds structurally related to cyanobacterin, most of which are related to anhydrocyanobacterin, including a dimer formed by [2 + 2] photocycloaddition. Two further analogues, previously reported following heterologous expression of the cyanobacterin biosynthetic gene cluster in <i>E. coli</i> as the nonchlorinated precyanobacterin I and II, were now isolated from the natural cyanobacterin producer. Cytotoxicity assays of cyanobacterin, anhydrocyanobacterin and one further isolated analogue showed only modest activity of the compounds against HCT116 cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2076–2089"},"PeriodicalIF":3.6,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.5c00591","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances in the Isolation, Bioactivity, Biosynthesis, and Total Synthesis of Hamigerans Hamigerans的分离、生物活性、生物合成和全合成研究进展。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-10 DOI: 10.1021/acs.jnatprod.5c00825
Xia Zhou, , , Jian-Hua Xie, , , Yao Jian, , , Xue-Song Gu, , , Yimou Gong, , , Dong Yi, , and , Ying Xiong*, 
{"title":"Recent Advances in the Isolation, Bioactivity, Biosynthesis, and Total Synthesis of Hamigerans","authors":"Xia Zhou,&nbsp;, ,&nbsp;Jian-Hua Xie,&nbsp;, ,&nbsp;Yao Jian,&nbsp;, ,&nbsp;Xue-Song Gu,&nbsp;, ,&nbsp;Yimou Gong,&nbsp;, ,&nbsp;Dong Yi,&nbsp;, and ,&nbsp;Ying Xiong*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00825","DOIUrl":"10.1021/acs.jnatprod.5c00825","url":null,"abstract":"<p >Hamigerans, a class of diterpenoid natural products isolated from marine sponge <i>Hamigera tarangaensis</i>, are characterized by distinctive 6–6–5 or 6–7–5 tricyclic skeletons. These compounds have been a focal point for synthetic chemists in recent years due to their remarkable biological activities. In this Review, we summarize the progress made in the isolation, biosynthesis, bioactivity, and total synthesis of hamigerans, with particular emphasis on synthetic studies published since 2013. Our goal for this Review is to provide new insights for future research on this class of marine natural products.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2259–2278"},"PeriodicalIF":3.6,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145032374","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Tetrasaccharide Resin Glycosides with Nitric Oxide Production Inhibitory Activity from Cuscuta campestris 菟丝子四糖树脂苷对一氧化氮生成抑制活性的研究。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-09 DOI: 10.1021/acs.jnatprod.5c00713
Jae Sang Han, , , Jun Gu Kim, , , Yong Beom Cho, , , Joon Su Jang, , , Vu Quan Dang, , , Dongho Lee, , , Mi Kyeong Lee, , , Jin Woo Lee, , and , Bang Yeon Hwang*, 
{"title":"Tetrasaccharide Resin Glycosides with Nitric Oxide Production Inhibitory Activity from Cuscuta campestris","authors":"Jae Sang Han,&nbsp;, ,&nbsp;Jun Gu Kim,&nbsp;, ,&nbsp;Yong Beom Cho,&nbsp;, ,&nbsp;Joon Su Jang,&nbsp;, ,&nbsp;Vu Quan Dang,&nbsp;, ,&nbsp;Dongho Lee,&nbsp;, ,&nbsp;Mi Kyeong Lee,&nbsp;, ,&nbsp;Jin Woo Lee,&nbsp;, and ,&nbsp;Bang Yeon Hwang*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00713","DOIUrl":"10.1021/acs.jnatprod.5c00713","url":null,"abstract":"<p >LC-HRMS/MS-based molecular-network-guided chemical investigation of <i>Cuscuta campestris</i> led to the isolation of seven undescribed tetrasaccharide-type resin glycosides (<b>1</b>–<b>7</b>). Their structures were elucidated using 1D and 2D NMR and HRESIMS analysis. Isolated resin glycosides were comprised of <span>d</span>-glucose, <span>d</span>-fucose, <span>d</span>-quinovose, and <span>l</span>-rhamnose, and these monosaccharides were partially acylated with acetyl, isobutyryl, <i>n</i>-hexanoyl, and niloyl organic acids. The absolute configuration of aglycones were determined as <i>S</i>-configuration using Mosher’s method after acid hydrolysis of resin glycoside fraction. All compounds were evaluated for their inhibitory activity against the production of nitric oxide in RAW 264.7 cells. Compounds <b>2</b> and <b>3</b> exhibited inhibitory activity, with IC<sub>50</sub> values of 14.3 and 10.4 μM, respectively.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2117–2126"},"PeriodicalIF":3.6,"publicationDate":"2025-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145022445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The Semisynthesis of 27-Deoxywithaferin A and 4-epi-5,6-Deoxywithaferin A from Withaferin A as Potential Antitumor Agents 半合成27-脱氧内夫林A和4-epi-5,6-脱氧内夫林A作为潜在的抗肿瘤药物。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-05 DOI: 10.1021/acs.jnatprod.5c00771
Yingfei Wang, , , Mingyue Lu, , , Yin Li, , , Xianxian Huang, , , Zhiling Liang, , , Yiheng Zhao, , , Hong Huang, , , Tingzhuang Yi*, , , Di Su*, , and , Zhiming Yan*, 
{"title":"The Semisynthesis of 27-Deoxywithaferin A and 4-epi-5,6-Deoxywithaferin A from Withaferin A as Potential Antitumor Agents","authors":"Yingfei Wang,&nbsp;, ,&nbsp;Mingyue Lu,&nbsp;, ,&nbsp;Yin Li,&nbsp;, ,&nbsp;Xianxian Huang,&nbsp;, ,&nbsp;Zhiling Liang,&nbsp;, ,&nbsp;Yiheng Zhao,&nbsp;, ,&nbsp;Hong Huang,&nbsp;, ,&nbsp;Tingzhuang Yi*,&nbsp;, ,&nbsp;Di Su*,&nbsp;, and ,&nbsp;Zhiming Yan*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00771","DOIUrl":"10.1021/acs.jnatprod.5c00771","url":null,"abstract":"<p >We describe two concise, three-step routes for the individual synthesis of 27-deoxywithaferin A (<b>2</b>) and 4-<i>epi</i>-5,6-deoxywithaferin A (<b>4</b>) from withaferin A (<b>1</b>). The protection strategy for the double bond of enone with thiophenol and the conjugate reduction of the epoxy group are important in generating these products, with an overall yield of 40%. The absolute configuration of 4-<i>epi</i>-5,6-deoxywithaferin A (<b>4</b>) has been confirmed by X-ray crystallography. 27-Deoxywithaferin A (<b>2</b>) exhibited a 400-fold higher potency than cisplatin against MCF-7 cells (IC<sub>50</sub> = 0.02 μM), while 4-<i>epi</i>-5,6-deoxywithaferin A (<b>4</b>) displayed variable IC<sub>50</sub> values (1.73–4.27 μM). Both compounds dose-dependently suppressed proliferation and induced apoptosis in MCF-7 cells, with 4-<i>epi</i>-5,6-deoxywithaferin A (<b>4</b>) demonstrating superior potency at higher concentrations. Notably, 27-deoxywithaferin A (<b>2</b>) significantly disrupted cell cycle distribution above 2.5 μM without dose dependence, whereas 5 μM 4-<i>epi</i>-5,6-deoxywithaferin A (<b>4</b>) induced phase-inconsistent cycle alterations. These findings highlight their antitumor potential and warrant further development.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2151–2157"},"PeriodicalIF":3.6,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145005664","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total Synthesis and Biological Evaluation of Moralbaflavone D 莫拉黄酮D的全合成及生物学评价。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-03 DOI: 10.1021/acs.jnatprod.5c00729
Ming-Ju Wen, , , Leiming Wu, , , Yi-Fan Fu, , , Dong Huang, , , Fang-Yu Yuan, , , Feng Wu, , , Jian-Kai Xia, , , Wei-Ye Wu, , , Tao Yuan, , , Jia-Luo Huang, , , Gui-Hua Tang, , and , Sheng Yin*, 
{"title":"Total Synthesis and Biological Evaluation of Moralbaflavone D","authors":"Ming-Ju Wen,&nbsp;, ,&nbsp;Leiming Wu,&nbsp;, ,&nbsp;Yi-Fan Fu,&nbsp;, ,&nbsp;Dong Huang,&nbsp;, ,&nbsp;Fang-Yu Yuan,&nbsp;, ,&nbsp;Feng Wu,&nbsp;, ,&nbsp;Jian-Kai Xia,&nbsp;, ,&nbsp;Wei-Ye Wu,&nbsp;, ,&nbsp;Tao Yuan,&nbsp;, ,&nbsp;Jia-Luo Huang,&nbsp;, ,&nbsp;Gui-Hua Tang,&nbsp;, and ,&nbsp;Sheng Yin*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00729","DOIUrl":"10.1021/acs.jnatprod.5c00729","url":null,"abstract":"<p >Moralbaflavone D (<b>4</b>) is a newly identified natural diprenylated flavonoid demonstrating cytotoxic activity. Herein, we report its first total synthesis, accomplished in only six steps with an overall yield of 5.1%. Key features in the synthesis included aryl ring prenylation, Claisen–Schmidt condensation, and intramolecular cyclization. Mechanistic studies have shown that <b>4</b> induces a G0/G1 phase arrest in a panel of cancer cell lines. The findings indicate that <b>4</b> exhibits moderate cytotoxic activity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2233–2238"},"PeriodicalIF":3.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144936125","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Mitrephorines A–E and Other Cytotoxic Aporphinoids from the Bark of Mitrephora tomentosa 毛毛白桦树皮中线粒体素A-E及其他细胞毒性类线粒体素。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-03 DOI: 10.1021/acs.jnatprod.5c00759
Watchara Sangsopha*, , , Paratchata Batsomboon, , , Chatphorn Theppitak, , , Surasak Prachya, , , Dhanushka Darshana, , , Chulabhorn Mahidol, , and , Somsak Ruchirawat, 
{"title":"Mitrephorines A–E and Other Cytotoxic Aporphinoids from the Bark of Mitrephora tomentosa","authors":"Watchara Sangsopha*,&nbsp;, ,&nbsp;Paratchata Batsomboon,&nbsp;, ,&nbsp;Chatphorn Theppitak,&nbsp;, ,&nbsp;Surasak Prachya,&nbsp;, ,&nbsp;Dhanushka Darshana,&nbsp;, ,&nbsp;Chulabhorn Mahidol,&nbsp;, and ,&nbsp;Somsak Ruchirawat,&nbsp;","doi":"10.1021/acs.jnatprod.5c00759","DOIUrl":"10.1021/acs.jnatprod.5c00759","url":null,"abstract":"<p >Six previously undescribed alkaloids, including three dimeric aporphine alkaloids, mitrephorines A–C (<b>1</b>–<b>3</b>), two aristolactam–aporphine alkaloids, mitrephorines D and E (<b>4</b> and <b>5</b>), and one 4,5-dioxoaporphine alkaloid, 8-methoxycepharadione A (<b>6</b>), accompanied by 13 previously identified compounds, were isolated from the bark of <i>Mitrephora tomentosa</i>. Their structures were determined by the analysis of UV, IR, NMR, and HRMS, while absolute configurations were assigned by chiral HPLC, specific rotation values, and ECD spectral data. Known compounds (<b>7</b>–<b>19</b>) were identified by comparison with literature data. The structure of mitrephorine A was verified by the analysis of single-crystal X-ray diffraction. Alkaloid dimers were isolated as mixtures of enantiomers (<b>1</b>–<b>3</b>) and atropisomers (<b>4</b> and <b>5</b>). Several isolates were evaluated against HuCCA-1, MOLT-3, HeLa, HepG2, T47-D, MDA-MB-231, S102, H69AR, HL-60, and A549 cancer cell lines, as well as the MRC-5 normal cell line. Compound <b>11</b> was active against MOLT-3 and HeLa cancer cell lines with respective IC<sub>50</sub> values of 4.5 and 5.1 μM, while compound <b>12</b> exhibited cytotoxicity against HuCCA-1 and MOLT-3 cancer cell lines (IC<sub>50</sub> values of 10.0 and 7.9 μM, respectively). None of the isolates were toxic against the MRC-5 normal cell line, with doxorubicin hydrochloride serving as the positive control.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2171–2180"},"PeriodicalIF":3.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.5c00759","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144990992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Bioactive Cyclodepsipeptides from Cocultured Mangrove-Derived Aspergillus sp. and Penicillium sp. 红树曲霉和青霉共培养的生物活性环沉积肽。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-02 DOI: 10.1021/acs.jnatprod.5c00752
Yu Wang, , , Guang-Ping Cao, , , Xin-Jian Qu, , , Yong-Hong Liu, , , Xiang-Xi Yi, , , Cheng-Hai Gao*, , and , Meng Bai*, 
{"title":"Bioactive Cyclodepsipeptides from Cocultured Mangrove-Derived Aspergillus sp. and Penicillium sp.","authors":"Yu Wang,&nbsp;, ,&nbsp;Guang-Ping Cao,&nbsp;, ,&nbsp;Xin-Jian Qu,&nbsp;, ,&nbsp;Yong-Hong Liu,&nbsp;, ,&nbsp;Xiang-Xi Yi,&nbsp;, ,&nbsp;Cheng-Hai Gao*,&nbsp;, and ,&nbsp;Meng Bai*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00752","DOIUrl":"10.1021/acs.jnatprod.5c00752","url":null,"abstract":"<p >Three new arthrichitin derivatives I–K (<b>1</b>–<b>3</b>) and three known congeners (<b>4</b>–<b>6</b>) were isolated from a coculture of mangrove-derived fungi <i>Aspergillus</i> sp. and <i>Penicillium</i> sp. using <sup>1</sup>H NMR-guided fractionation. Their structures were determined by comprehensive spectroscopic analysis (1D/2D NMR, HRESIMS, ESI-MS/MS), Marfey’s analysis, DP4+ probability, and experimental/computed ECD comparison. All compounds were evaluated for antibacterial effects and cytotoxicity. Notably, compounds <b>1</b> and <b>5</b> showed weak cytotoxicity against MHCC-97H cells (IC<sub>50</sub> = 20.1 ± 0.9 and 25.8 ± 0.4 μM, respectively). Compound <b>4</b> exhibited potent anti-BPH activity (IC<sub>50</sub> = 0.36 ± 0.02 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2239–2246"},"PeriodicalIF":3.6,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144936120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cytotoxic Lignan and Flavonoid Derivatives from the Branches of Beilschmiedia yunnanensis 云南贝氏枝中具有细胞毒性的木脂素和类黄酮衍生物。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-02 DOI: 10.1021/acs.jnatprod.5c00778
Korydwen Terrasson, , , Ermias Mekuria Addo, , , Manead Khin, , , Tran Ngoc Ninh, , , Pankaj Pandey, , , Amar G. Chittiboyina, , , Daneel Ferreira, , , Harinantenaina L. Rakotondraibe, , , Joanna E. Burdette, , , Djaja D. Soejarto, , and , A. Douglas Kinghorn*, 
{"title":"Cytotoxic Lignan and Flavonoid Derivatives from the Branches of Beilschmiedia yunnanensis","authors":"Korydwen Terrasson,&nbsp;, ,&nbsp;Ermias Mekuria Addo,&nbsp;, ,&nbsp;Manead Khin,&nbsp;, ,&nbsp;Tran Ngoc Ninh,&nbsp;, ,&nbsp;Pankaj Pandey,&nbsp;, ,&nbsp;Amar G. Chittiboyina,&nbsp;, ,&nbsp;Daneel Ferreira,&nbsp;, ,&nbsp;Harinantenaina L. Rakotondraibe,&nbsp;, ,&nbsp;Joanna E. Burdette,&nbsp;, ,&nbsp;Djaja D. Soejarto,&nbsp;, and ,&nbsp;A. Douglas Kinghorn*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00778","DOIUrl":"10.1021/acs.jnatprod.5c00778","url":null,"abstract":"<p >An investigation of a cytotoxic MeOH extract of the branches of <i>Beilschmiedia yunnanensis</i>, collected in Vietnam, led to the isolation of four new compounds (<b>1</b>–<b>4</b>). Two of these, isolated from a CHCl<sub>3</sub>-soluble partition, were characterized as the furofuran-type neolignans, beilschmiedianins A (<b>1</b>)[(7<i>R</i>,7<i>′R</i>,8<i>S</i>,8′<i>S</i>,8″<i>R</i>)-4′,4″,9′′-trihydroxy-3,5,3′,3′′-tetramethoxy-4,8′′-oxy-7,9′:7′9-diepoxy-8,8′-sesquilignan-7′′-one)] and B (<b>2</b>) [(7<i>R</i>,7′<i>R</i>,7″<i>R</i>,8<i>S</i>,8′<i>S</i>,8″<i>R</i>)-9″-feruloyl-4′,4′′-dihydroxy-3,5,3′,3′′-tetramethoxy-4,8″-oxy-7,9′:7′,9-diepoxy-8,8′-dilignan-7″-ol]. In turn, the flavonoid glycosides <b>3</b> and <b>4</b> were obtained from an EtOAc-soluble partition and were assigned as (2<i>R</i>,3<i>R</i>)-dihydrokaempferol-5-<i>O</i>-β-<span>l</span>-arabinosyl-(2→1)-α-<span>l</span>-rhamnopyranoside and (2<i>R</i>,3<i>R</i>)-dihydrokaempferol-5-<i>O</i>-β-<span>l</span>-arabinopyranoside, respectively. The structures of these new compounds were determined using a combination of spectroscopic and spectrometric methods. Additionally, the known dilignan, (−)-9,9′-<i>O</i>-diferuloylsecoisolariciresinol (<b>5</b>), showed selective cytotoxicity against the OVCAR3 ovarian cancer cell line, with an IC<sub>50</sub> value of 0.51 μM. Mechanistic studies showed that compound <b>5</b> increased the cPARP levels and decreased the expression of BCL-2 in OVCAR3 cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2158–2170"},"PeriodicalIF":3.6,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144936082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Lindenane-Based Sesquiterpenoid Hetero-Oligomers with Diverse Skeletons and Extracellular Regulated Protein Kinases Inhibitory Activity from Sarcandra glabra 具有不同骨架和胞外调节蛋白激酶抑制活性的椴树烯基倍半萜类杂聚物。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-09-01 DOI: 10.1021/acs.jnatprod.5c00785
Danyang Zhang, , , Zhiqi Xiao, , , An Huang, , , Pengfei Tang, , , Houli Jiang, , , Mengmeng Yu, , , Ze Zheng, , , Lingyi Kong*, , and , Jun Luo*, 
{"title":"Lindenane-Based Sesquiterpenoid Hetero-Oligomers with Diverse Skeletons and Extracellular Regulated Protein Kinases Inhibitory Activity from Sarcandra glabra","authors":"Danyang Zhang,&nbsp;, ,&nbsp;Zhiqi Xiao,&nbsp;, ,&nbsp;An Huang,&nbsp;, ,&nbsp;Pengfei Tang,&nbsp;, ,&nbsp;Houli Jiang,&nbsp;, ,&nbsp;Mengmeng Yu,&nbsp;, ,&nbsp;Ze Zheng,&nbsp;, ,&nbsp;Lingyi Kong*,&nbsp;, and ,&nbsp;Jun Luo*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00785","DOIUrl":"10.1021/acs.jnatprod.5c00785","url":null,"abstract":"<p >Sarcglabtenes A–G (<b>1</b>–<b>7</b>), seven lindenane-based sesquiterpenoid hetero-oligomers with six unprecedented skeletons, along with five new biosynthetic analogues sarcglabtenes H–L (<b>8</b>–<b>12</b>), were isolated from <i>Sarcandra glabra</i>. Their structures including absolute configurations were comprehensively elucidated using HR-MS, NMR, ECD, and single crystal X-ray diffraction. Structurally, sarcglabtenes A–G are lindenane hetero-oligomers including a geranyl homogentisic acid (<b>1</b>/<b>2</b>), geranylgeranyl <i>p</i>-toluquinone (<b>3</b>/<b>4</b>), germarane (<b>5</b>), campholenal (<b>6</b>/<b>7</b>) derivatives, for which plausible biosynthesis pathways are also proposed. In bioassays, <b>1</b>–<b>4</b> exhibited cytotoxic activity against five cancer cell lines, and in particular, <b>4</b> acted as extracellular-regulated protein kinase (Erk) inhibitor of the MAPK signaling pathway involved in apoptosis.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2181–2192"},"PeriodicalIF":3.6,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144936160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
seco-Tirucallane Triterpenoids from the Leaves of Dysoxylum gotadhora 山茱萸叶中二羟基三萜的研究。
IF 3.6 2区 生物学
Journal of Natural Products Pub Date : 2025-08-31 DOI: 10.1021/acs.jnatprod.5c00360
Hui-Jiao Yan, , , Ming-Ye Li, , , Jia-Le Zhou, , , Yan-Ling Geng, , and , Xiao Wang*, 
{"title":"seco-Tirucallane Triterpenoids from the Leaves of Dysoxylum gotadhora","authors":"Hui-Jiao Yan,&nbsp;, ,&nbsp;Ming-Ye Li,&nbsp;, ,&nbsp;Jia-Le Zhou,&nbsp;, ,&nbsp;Yan-Ling Geng,&nbsp;, and ,&nbsp;Xiao Wang*,&nbsp;","doi":"10.1021/acs.jnatprod.5c00360","DOIUrl":"10.1021/acs.jnatprod.5c00360","url":null,"abstract":"<p >Thirteen new 3,4-<i>seco</i>-tirucallane triterpenoids (<b>1–11</b>, <b>15</b>, <b>16</b>), along with one new 2,3-<i>seco</i>-tirucallane triterpenoid (<b>17</b>), one new 3,4-<i>seco</i>-29-nor-tirucallane triterpenoid (<b>12</b>), one new 3,4-<i>seco</i>-28,29-dinor-tirucallane triterpenoid (<b>13</b>), and a known tirucallane analogue (<b>14</b>) were isolated from leaves of <i>Dysoxylum gotadhora.</i> These triterpenoids were structurally determined by spectroscopic methods, including HRESIMS, NMR spectroscopic analyses, single-crystal X-ray diffraction, and ECD data. The cytotoxicity evaluation revealed that compounds <b>4</b> and <b>11</b> exhibited moderate activity against HCT-116 and DLD-1 cell lines with IC<sub>50</sub> values ranging from 3.7 to 4.4 μM. The Annexin V-PE/7-AAD staining assay indicated that both <b>4</b> and <b>11</b> induced apoptosis in a concentration-dependent manner. Further studies showed that compounds <b>6</b>, <b>9</b>, <b>10</b>, and <b>17</b> exhibited suppression effects on NO production in LPS-induced RAW 264.7 cells, with IC<sub>50</sub> values ranging from 17.1 ± 3.3 to 49.8 ± 6.5 μM.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2041–2052"},"PeriodicalIF":3.6,"publicationDate":"2025-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144935986","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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